Two Big Questions to Guide the Year

January 3, 2025 — Two Questions to Guide the Year

Welcome back. I hope you’re rested and enjoyed time with family and friends. (I wrote this somewhere in Kansas on my drive to Colorado.)

This letter is about two questions that I believe can help us map the year ahead. Together they can guide a department, individual teams, and small groups — and most powerfully, your own work, when no one else is looking.

1. What would this look like if it was easy?
2. What would great look like?

Q1: What would this look like if it was easy?

We have big work ahead. Finding a starting point is impossible when you think you have to eat the proverbial elephant in one bite. Before taking on a new project or having a difficult conversation, try reframing by asking: What would this look like if it was easy?

This doesn’t mean we shy away from challenges or challenging work. Instead, we look at what really matters and what would need to be true for it to feel easy. For something small, we might realize it’s actually easier than we first thought. Other challenges are still big but can be broken down. The answer to “What would running a marathon look like if it was easy?” might be: running a few times a week for 12+ months, having a running partner, and setting a goal of finishing in 5 hours.

(You can also apply this question in reverse: what would this look like if I made it as hard as possible?)

When I’ve used this question in my own work, it helps me slow down and take a breath. Then I feel like I have time to zoom out and see a project or problem with better perspective. It’s not magic but it’s close. It helps me see the first step and then the next. It also gives permission — permission to think about what you control, what resources, people, and information you’ll need before you dig in.

Best of all, it allows you to imagine a path that is easy and that makes good work feel light.

Q2: What would great look like?

If the first question is about helping us get started and see the path forward, this one is about being clear about strategy and objectives — and imagining the quality of our work, not merely its completion.

How do we even know what great is? We’ve all seen great work before, created by ourselves and by others. We know it because we have a keen eye for when it’s missing in someone else’s work. It’s often much harder to see when it’s missing in our own.

The goal in asking this question isn’t to point a finger or challenge someone else’s work. It’s to challenge our own work and our part in it. To put it another way: What would great look like for me?

When you ask that question, you’re holding up a mirror.

Making it actionable

Apply the questions to the task of making these questions actionable. What would make it easy to use them? And what would great look like when using them?

First, to make it easy: at the start or end of a meeting, ask the questions out loud. Write them on a notebook or the whiteboard. Hold each other accountable.

Second, what would great look like in using these questions? They can help you do better work through self-reflection. Ask yourself before you start your day. Ask after a meeting what you could do to make it easy and great for others. Keep a running list of where you think you overcomplicated something or fell short.

What does that look like?

• Coming prepared to a meeting with a plan, having simplified what you want to say to make it easy for others to listen
• Summarizing your points and asking for clear actions or feedback
• Listening to others when they speak
• Making your next steps clear and communicating your progress — or roadblocks — along the way
• Saying out loud what you are going to do better next time
• Following through on what you said you would do

So what will the year look like? Let’s aim for a year of putting ourselves in the best position to do great work.

— T.V.